


Deep Water

by hellofromthecity



Series: Coney Island Baby [1]
Category: Gilmore Girls
Genre: Angst and Romance, Banter, F/M, Implied/Referenced Child Abuse, Season/Series 04, What-If
Language: English
Status: Completed
Published: 2020-05-06
Updated: 2020-06-03
Packaged: 2021-03-02 23:26:55
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 9
Words: 15,211
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24035032
Author URL: https://archiveofourown.org/users/hellofromthecity/pseuds/hellofromthecity
Summary: "There was only one person who made him feel that he was more than his baggage. She was a beam of light cutting through the Hudson River, and he was reaching for her like he promised he wouldn’t."Jess tries his best to stay away, but it doesn't last. A what-if where Rory runs away with him (on her terms), and Jess starts to figure out his shit.
Relationships: Rory Gilmore/Jess Mariano
Series: Coney Island Baby [1]
Series URL: https://archiveofourown.org/series/2152563
Comments: 26
Kudos: 71





	1. 1

He was a wreck. It wasn’t something he could ever say out loud. He could barely think it. But as he barreled down the highway with _I love you_ ringing in his ears... _IloveyouIloveyouIloveyou..._ he knew a screw had come loose. That’s what she did, an angel-faced screwdriver, working at him till he came undone.

He turned on the tape deck, ‘Guns of Brixton’ playing its first notes. 

“Oh fuck off.”

The radio it is. A cheesy Hartford classic rock station quickly turned to static. 

It wasn’t that big a deal to be a fuck up if noone stuck around to be collateral damage. That’s what she was, Luke too. Both puppy-eyed chumps caught in the crossfire of his angst. 

Driving one handed, he rustled through his tape box, looking for something terrible and loud. Anything to drown out the self pitying drivel in his head. He slapped something in, realizing too late it was a mix Shane made him that hazy, long lost summer. _Whatever._ Volume blasted, he finally merged onto a freeway. But there it was, impossible to drown out: _IloveyouIloveyouIloveyou…_

The exit for New York was miles ago. He had driven through the night, and met the morning in bumfuck nowhere. The sun was rising over the Susquehanna river. Jess pulled onto a small dirt lot in front of a watering hole, as the morning went from freezing to frigid, and slept. 

He woke up to the sound of rushing water and a crick in his neck. His windshield was frosty. What was he doing? Running from a small town to the boonies. It was well into the day, maybe two. He got out of the car and stood above the river, lighting up his second to last smoke. He wasn’t running from Stars Hollow, but the hurt he left there. No one would believe it, but he was more relaxed there–when Luke and Rory could put up with his bitter attitude long enough to have a couple laughs with him. It was secure. But in the end they couldn’t handle him. Noone could, so fuck it. 

“Fuck it,” he said aloud with a puff of smoke, even though the words felt wrong. 

Jess got back in the car. He rolled down the window and put on ‘Guns of Brixton’, driving back where he came with a bracing gust of air and a bass intro that plucked melancholy in his stomach. 

…

He kept his head down. He moved into a New York shithole, got a job that kept him moving, and went through the motions. The plan was to ignore it. _It_ being everything in him that burned hot, that made him say stupid shit and abandon people. 

When he wasn’t exploding with angry tirades or love confessions, he was usually busy being an angsty little prick. That was fine. He could manage being an angsty little prick. And if at night he went somewhere where the music threatened to burst his eardrums and threw back enough whiskey to tranquilize a small horse, that was fine. If he walked all night into the early morning, smoking like a chimney, that was fine. He was always up for work in the morning with a clean shirt on his back. He was a fucking pro. 

Anything to keep that heat in him from bubbling into something he couldn’t control–a rage or a love that took him over completely. 

Then Luke pounded on his front door, and all that went to shit. 

…

She wasn’t there. But the echo of her was. Lorelai gave him unreadable sideways glances while she thought he wasn’t looking. It made him itch. Rory had left pieces of herself in the apartment above the diner, her light blue cardigan was draped over the chair. A book she had obviously leant Luke sat on the kitchen table. _The Pearl_ by Steinbeck. Perfect for Luke. Nice and short. The book felt familiar in his hands, like all of her books did. He didn’t dare touch the sweater. One, it would make him a total creep. Two, he could still remember what it felt like, what she felt like in it. Lanky and soft and _safe._

He was trying to keep his shit together, not give anyone anything to talk about, but it didn’t help that his mom was all over him. His mom was apparently playing the role of the town ditz. New York Liz was hardly so charming. But in a way he was happy for her. She really cleaned up, as much it made his stomach churn to see her flouncing around–rosy cheeked–when he only got flashes of that Liz in his youth. 

The town talked shit when he walked through the square. But they always talked shit. Nevertheless he was getting tenser by the minute. So getting into a fight with TJ at a strip club was a given. 

Later that night, with only bedside lamps illuminating Luke’s apartment, Jess finished his reread of _Virgin Suicides._ He closed the book and tossed it on top of his duffel, reflecting on ‘It didn’t matter in the end how old they had been, or that they were girls, but only that we had loved them, and that they hadn’t heard us calling.’

“You seem...different then when I saw you last.”

Jess looked up in surprise. He thought Luke had dozed off, but he was looking at him inquisitively from his bed.

“Don’t get me wrong, not that different. You still started a brawl at a strip club. But you’re a little less...caustic.”

“Wow. 'Caustic'. Impressive," Jess mocked.

“Nevermind. I take it all back.”

“Sorry. Thanks, I guess. I’ve been uh–” Jess ironically struggled to find the right word. “–marinating.”

Luke furrowed his brow at that. 

“Huh. Well...I'll be sure to throw you on the grill in the morning. I'm sure Ms. Patty would order seconds.”

Jess smirked as Luke switched off his light and turned over to sleep. 

The next day he walked Liz down the aisle and it only half as painful as he thought it would be. And he almost felt happy, watching her marry that dunce. But it was still there, simmering under the surface. The hurt. The wanting. Everything that made his fists clench. 

...

The appraising look in Luke’s eye before Jess left reminded him of Liz’s second husband. Jess didn’t necessarily like him, but he was tolerable. And Liz only smoked weed and drank lite beer while she was with him, making for a mellower couple years while they were together. 

He was older than Luke, grumpy and not good with kids. But he just sat in the living room with a beer and a scowl, listening to Townes Van Zandt records. Harmless, charming even–compared to the rest of the pack. Jess was twelve when he died. A week before he kicked the bucket, Jess remembers standing awkwardly in the hospital room. He didn’t know what he was supposed to feel and he didn’t feel much at all. They were waiting in silence for Liz to finish her joint in the hospital parking lot. He stared at Jess with his typical scowl. Jess shoved his hands into his pockets. Sighing from his hospital bed, he said something Jess never forgot. 

“You’re in deep water kid.”

A week later he passed in his sleep. A month later Liz was scrambling for rent money–arguing with Luke on the phone while Jess ate noodles with ketchup and reading _Trout Fishing in America_ . Three months later Liz was dating a jewelry shop clerk that gave her coke and Jess fare hopped onto the subway, reading _The Heart is a Lonely Hunter_ in Washington Square Park. 

Jess knew where he was going. ‘Cause there was only one person he wanted to tell all of this even though he would never know how. There was only one person who made him feel that he was more than his baggage. She was a beam of light cutting through the Hudson River, and he was reaching for her like he promised he wouldn’t.

...

“No!”

He turned to leave, everything in him seizing with a grief that made him want to smoke a whole Malboro Reds factory. 

“You’re just gonna leave again, without a word?”

He stopped in her door frame. 

“Professing your love isn’t the same as an apology, so I'm still waiting on one! Turn around.” 

He did, and took a small step back into the living room. She looked strong and volatile, with eyes ablaze and her shoulders tensed in anger. 

“I mean, where did you even run to?”

“New York.”

“What have you been doing with yourself?”

Jess shrugged. Rory scoffed and rolled her eyes. 

“Flying without a net.”

That stopped her. His eyes gleamed, raw. It was vague, but it was honest. 

“Meaning what?”

_I’m lost._

He looked at her, chewing the inside of his cheek. He had no idea how to say what he wanted to say, what he had been burning to say for months. 

“Well?” she demanded. 

“I’m sorry. I’m sorry I can’t tell you what you want to hear. I don’t know how to explain myself to you. I don’t want to be this mess that keeps fucking up your life, but...you’re all I want. Everything else is…muted. And I don’t know what to do about it”

He was close to hitting his limit. Feet itching to run. Fists clenching, unclenching. 

“I’m not going to run away with you,” she started, breaking eye contact with him. She looked a semblance less sure of herself. 

“But?”

Rory said nothing, just covered her face with her hands. There was something different about her, not only in the sharpness of her jaw but in how she held herself. Something was weighing her down. 

“You want to run. I can tell.”

“You don’t deserve it! For me to just fall into your arms!”

“I know that! But what do _you_ want?”

“Answers. I want to know why I’ve been walking through the day for the last year with this pain lurking under the surface, this unfinished business. I want to know why, when I lay down at night, it all comes back, and it’s as if you just left without saying goodbye–all over again.”

All Jess could do was look at her, helpless. 

“Well say something!”

“So what do you wanna do, drive, walk around, hash it out _Mikey and Nicky_ style?”

“Yes,” she decided firmly.

He would take what he could get. He was shocked to get his much, all things considered. 

“Okay.”

They stared at each other, half like strangers half like lovers. 

“I’m going to grab some clothes. A toothbrush.”

Jess nodded, eyes still burning bright and dangerous. Rory let out a shaky sigh and went to her room to pack, lightheaded with the urgency of it, the recklessness of it. She looked at all the boxes in piles, and told herself they could wait a few days. 

She looked back at him, standing in her living room, fiddling with the zipper on his jacket. He didn’t know she was looking. He looked young, small even. She knew it shouldn’t, as she shoved some t shirts in her backpack, but it felt right.

  
  
  



	2. Chapter 2

Jess was afraid to say anything, that it might make her change her mind and demand he take her back. Everytime he turned on the tape-deck or the radio she turned it off. A punishment perhaps, but he doubted she enjoyed the silent tension either. He struggled to find something to diffuse it. Jokes evaded him. Their silence was usually comfortable, it had to be as his conversational stamina was spotty at best. But this was something else. 

Rory sat rod-straight. She kept lifting her eyebrows up and down, trying to get the muscles in her face to relax. Being in his car was like entering a time machine. Except instead of listening to albums with his head in her lap, or making out–sweaty and exhilarated–after the Distiller’s concert, they both sat like there was a wild animal in the car, and if they made any sudden movements it would attack. 

“Rory–”

“Just drive.”

“Okay.”

And drive he did. They ambled down the I-95 for miles, theoretically for New York. But neither of them were very forward thinking at the moment, instead levitating in the painful exilieration of each silent second. 

Then she saw it, a gleaming salvation in the darkness. The green highway sign read: _Mystic Seaport 1 mile._

“Take the next exit.’

“What?”

“Just do it!”

“Is that the town from _Mystic Pizza_?”

“Yes!” she answered, annoyed. 

“You’ve got to be kidding me.”

“Who’s the boss?” she snapped.

Jess smirked as he took the exit, turning into the harbor town. 

“You’re the boss.”

They sobered into silence again as Jess drove in circles looking for a Motel that wouldn’t give them bedbugs or empty his already sparse wallet. He finally saw a rundown, retro sign for a place called _The Stardust Motel._ It blinked at them in white and red while Jess idled in the parking lot. 

“Is this okay?”

“As long as it doesn’t charge by the hour,” she bit.

“Good one.”

She got out of the car as soon as he pulled into a spot and practically stormed towards the lobby. Jess chased her, feeling a twinge of dejavu. 

In the lobby she shifted her weight from foot to foot, clutching the straps of her backpack. She realized how young she must look and stilled, but Jess caught it–giving her a fond glance that made her breath catch in her throat. 

“One bed or two?” the bedraggled receptionist asked. It was the dreaded question.

“Uh, two.”

Rory was almost disappointed, even though he gave the gentlemanly answer. She mentally scolded herself for wanting _it. H_ _im_. 

They dropped their meager belongings off at the room, which was very old, very tacky, and very red. 

“Walk?” Jess asked. 

“Huh?” 

“Do you want to walk? I know it’s late…” 

“Sure. Let’s walk.”

They strode onto the dark empty streets of Mystic. The thick, cold smell of ocean guided them towards the harbor, past cobbled streets of shop windows. 

Rory was agonizing over the conflict of her decision, of how much she resented him and how unsustainable that resentment was now that he was standing in front of her. She hated herself for it, for how she wanted to slide her hands under his jacket and just _lean in_. 

The room cost fifty five dollars. That was a third of the money Luke left him. Jess told himself it was worth it, that it had to be. But Rory was icing him out in a way she never had before. Red-cheeked Rory, blustering with anger–that at least was familiar. Since she got in the car she was totally unreadable. His head snapped up when she finally broke the silence. 

“My mom took me here when I was in middle school. Mystic Pizza was my favorite movie at the time. She took me out of school and said I had an appointment with the dentist, and took me here instead.” 

“Why bring me here?” Jess asked, regretting it as soon as he did, based on the twist of her mouth. 

“I don’t know. It’s familiar. Maybe it’s sacrilegious to bring you into this happy and simple childhood memory I shared with my mom.”

The ocean came into view, the muted roar of its waves getting louder. They stopped on the pier, leaning against the railing and over the dark water.

“I’m still angry at you Jess. And for the record I think storming into my living room and asking me to run away with you is a ridiculous and selfish gesture, and don’t think for a second that I’m not going to back to Yale,” Rory started, heating up again. 

This time her words instilled more than a helpless sadness in him. His brows furrowed in irritation.

“Then why did you come?” 

His words come out harsh, shocking Rory into looking at him. Really looking at him. He was impossibly still, eyes intense and lit by the harsh light of the street lamp. All of him was locked onto her.

She stammered.

“Because...I need to understand what made you hurt me.”

_Because when you said you loved me it was like getting hit by lightning. Because I’m unhappy. Because I was on the verge of doing something stupider than run away with you._

His face didn’t change, still that hard inquisitive look that people who didn’t know him misinterpreted as a glare. Why was it always like this? They could never just say what they meant. Neither of them. 

He knew her answer was incomplete. He wanted to reach for her elbow, give that small touch that used to be so habitual for him.

“Why did you come back?” she asked him, with less anger this time. 

“Isn’t it obvious?” 

Right. He was in love with her. In that way, despite there being so much she didn’t know, he was the one with his cards on the table. 

They stared at the murky waves, returning to silence. Jess gave a shaky sigh. He had to give more than that to hold on to their tenuous truce. He kept trying to get the words out, resulting in a series of silent false starts. He screwed his eyes shut, 

“I left the first time to see my dad. But also because I felt that I had been building up to something. A fall. And I didn’t want you to see it. I didn’t want anyone to see it.” 

He said it as clear and strong as he could, but his breath came out obvious and shaky after the last word. He looked at her, found her face open for the first time in a long time. 

She took in his words, took in his face that pleaded _This is me trying. I know it’s an inch. Please don’t take a mile._ Her anger melted, and she let her body lead. It was like a current, how she drew him in tight–burying her face in his neck. He brought his arms around her, his cheek to her hair. it wasn’t forgiveness. But it was firm, and it was good.

**Notes for the Chapter:**

> Next chapter should lighten up a bit.


	3. Chapter 3

They made it back to the motel and got ready for bed in an exhausted but almost amiable silence. There was a silly feeling about sleeping apart, something stilted about how Rory went to the bathroom to change, and he pulled his jeans off while she wasn’t in the room–slipping under the covers. He wanted to laugh. Touch came so easy for them. 

They held onto each other for a long time at the harbor, not wanting to leave the haven they had created in their embrace. But back to the cold wet wind of Mystic at night. Back to the charged silence, as they walked to the motel. Now they laid in separate beds, something unfinished.

A fall. He had called it a fall. That was one way to put it. When he first got to LA, things were alright. They weren’t great, but he had a routine. He would sleep on the mattress in the living room, work at the hotdog stand, try and at least nod at Jimmy’s rambling jokes. Then he started wandering, sitting alone at bars till he wasn’t sitting alone. The women, usually older, would touch his cheek. They wanted him, and it always came off as tender even if it wasn’t. They would stroke his back. He would fuck them without making a sound and they would laugh. _What, are you embarrassed?_ A woman named Nina once asked him. He put his mouth to good use so she wouldn’t ask any more questions. There was nothing wrong with it–with sleeping with them. But then he stopped sleeping at all. He would walk all night–spend all his cash on cigarettes. And the touch stopped being fun. Sometimes when they would cup his face, touch his hair, he would feel so young and so raw. But he kept doing it until Jimmy kicked him out. Ironic since he was never there. 

God he needed a smoke. He slid out of bed and rustled around for his jacket and jeans, trying to be quiet even though he knew Rory was awake. He grabbed his key card key from the side table and slunk out, sliding his arms into his jacket. The lighter flicked, the smoke flowed, and he closed his eyes to the headrush. He didn’t feel like shit, like in LA or New York where everything sent him toppling into some fucked up coping mechanism. He just felt _intense_. Like when a song you’ve heard a billion takes you by surprise. For three minutes it possesses you, and the song is all you can feel. Rory was definitely possessing him. 

With a soft click the door to their room opened and Rory stepped into the cold parking lot. She looked him up and down. Bare feet, pants unbuttoned, hair soft and messy, eyes dangerous as always. She was in her socks, sweatpants, and a Cher t-shirt she stole from her mom. She didn’t know it, but her eyes were dangerous too. He liked her like this, rumpled and soft. 

“Can’t sleep?” Jess asked between drags. 

“No.”

 _What do you want?_ He had asked her. The question never left her mind. She watched him smoke in his leather jacket, somehow not a cliche. She hugged herself against the cold, skin tingling. But her cheeks were hot.

“When did you start smoking?”

“Fifth grade school field trip. A girl named Maddy Vu found half of one on the ground at the park and dared me to smoke it. I had one of Liz’s lighters in my backpack, cause I thought it made me cool. Took the dare. Maddy Vu was my first kiss.”

Rory walked closer to him, smiling. 

“That’s not what I expected.”

“Not everything’s a sob story.”

Jess was half way done with the cigarette, breathing slowly, looking calmer. He stared at her without worry, almost playful. She recognized it for what it was. She felt it in her face too. Desire. 

“Can I try?” she asked, gesturing at the cigarette.

He barked a surprised laugh.

“What, so your mom can throw flaming darts at me instead of my picture?”

“Come on!”

Jess rolled his eyes. 

“Alright, guess everyone’s gotta raise a little hell.”

He handed it to her, careful she wouldn’t burn her fingers on the cherry. She held it to her mouth, and tried to breathe it in easy like he did. It was savory, and harsher than she expected. She only managed to hold it in for a couple seconds before coughing. Jess took it from her, laughing fondly. 

“Not for me,” Rory said through her coughs. 

“Good riddance.”

Jess casually put his hand on her back while she coughed, rubbing up and down while he finished the cigarette. She looked up and shivered, locked eyes. He flicked the butt, his hand starting to grip the fabric of her shirt. Her hand came up to his, traveled up his arm, his bicep through the leather. This touch wasn’t like at the pier. It wasn’t an offering. It was about taking. His hand fell to her waist and pulled. 

There was a growl at the back of his throat waiting to come out. This was different from the one night stands for obvious reasons. He wasn’t scratching an itch. Pulling her into him was a compulsion. Before he knew it she was sliding her hands under his shirt up his back, slow and steady, still looking at him with those eyes. 

She kissed him with no hesitation. She knew what she wanted. He responded in turn like he always did, kissing her like it was the last time cause that was his style. Make it addictive. Make it sweet. Make it hurt. His mouth fell to her clavicle, teeth brushing the skin there. She gasped and pulled at his hair, stopping him, remaining close. He stilled, breathing hard like an animal posed to strike. With one last brush of her lips against his hair, she pulled back. 

“Just that for now,” she breathed. A laugh bubbled in her. He looked flustered, eyes black. She sauntered back to the room. 

He watched her leave, trying to catch his breath.

“Fuck.”

  
  


**Notes for the Chapter:**

> I swear next time they'll actually go out and do something! But I couldn't have them just...go to bed.


	4. Chapter 4

**Notes for the Chapter:**

> Downright cutesy.

At eight Rory woke up ravenous. She sat up and looked over at Jess’ bed, where he lay, a lump under his blankets. Poking softly at first, she whispered his name. When he didn’t respond, she started to peel the blanket away from his face and he groaned, awake. 

“I’m starving.”

He didn’t respond, giving her a sleepy scowl and stretching like a cat. 

“You’re not starving,” he muttered, voice rough with sleep. 

“Semantics! Now get up, it’s coffee time.”

He rolled onto his belly, burying his face in the pillow. 

“Okay. I’m gonna take a shower, and when I’m done I want you powdered, clothed, and ready to rumble!” she said with ridiculous pep, somehow still on a power high from the night before. 

“Ugh. You sound like a soccer mom.”

Eventually he dragged himself out of bed, changed into semi-clean clothes, and ran a hand through his too-long hair. Rory popped out of the shower, squeaky clean and wrapped in a towel. He busied himself with tying his shoes, giving her the chance to change. He brushed his teeth and put on some Old Spice–his new baseline for hygiene, and they were out the door. He almost forgot before stopping, slightly embarrassed. 

“Hey, Rory, are we staying another night? Check out’s at eleven.”

“I have a few days till I have to move my stuff out of the dorm, so I was thinking yes?” 

He shuffled a bit. Money or lack thereof was a real damper on the spontaneity of whisking her away. 

“Um, I can’t really afford…”

Rory slapped her forehead, so used to how he would pay for everything. But that was food, and books, concert tickets, and he had stability. Now he was a real vagabond, without an uncle to back him up.

“Oh! Of course! I got tonight. We’ll go dutch.”

“Sorry,” he started sheepishly.

“Jess no, we’re adults. And feminists at that. I’ll pay for the room.”

Still good natured and more energetic than he, she went into the lobby to book them another night. After, they made their way to breakfast

Mystic was decidedly quaint and as touristy as any of the Connecticut beach towns. But it still had those working class, harbor-economy bones, so Jess could tolerate it. Maybe it was too precious for his tastes, bu there was a total anonymity to it. 

“You’re really letting that go, huh?” Rory asked playfully. 

“What, my hair?”

“Yeah your hair. You going for a George Harrison look?”

Jess rolled his eyes. 

Rory made a left turn, apparently already having a destination in mind. 

“I live a demanding life! And I’d never aspire to hippiedom.”

“He was the coolest Beatle!”

“He was a Hare Krishna.”

“So was Ginsberg!”

“Ginsberg gets a pass, obviously. Besides, I was never much of a Beatles fan.”

“Ugh. You contrarian rocker you.”

“What, you a mod?”

Rory stopped in front of a cafe, looking back at him as she pushed the door open. 

“No! I’m a mocker!”

As Rory practically skipped to the counter to order, Jess snuck an earnest smile at her good mood.

The cafe was casual, and close enough to the water that you could hear it. It was all unvarnished wood, homey flower arrangements in tin cans on the tables. They took a number and sat by the window. Jess got a coffee and a simple egg sandwich. Rory ordered a big plate of waffles with strawberries, a side of sausage, and of course, coffee. 

He looked at her with laughter in his eyes, nibbling at his sandwich. She ate with relish, as always. It was a Gilmore cliche, but it never ceased to make him smile, the unbridled–almost perverse–enjoyment of her food. 

“Is that really all you’re gonna have?” she asked incredulously. 

He kept it to himself that he would rather not blow his meager funds on a lavish breakfast. 

“What can I say, I’m low maintenance.”

“Well live a little!” she insisted, slapping half of one of her waffles on his plate, scooping some strawberries on top for good measure. 

“Thanks.”

She smiled and continued to inhale her food.

“So what’s got you so peppy?” 

Rory didn’t realize it till he said it. She was peppy. In fact she had more energy than she had in weeks, despite only sleeping around five hours. Funny, considering how angry she was at herself yesterday for even coming with him. But all drama aside, she was happy in the escape, happy with him. She could be happy without too–but there was a freedom when she was with him that swung between danger and total contentment. 

“I dunno,” she responded. Even though she did know. “I’ll think on it.”

“You do that,” he responded carefully. There was something different about her, foreign from their time together in high school. 

“Hey, what are you reading lately?” she was shocked she hadn’t asked sooner. This was their bread and butter. 

“I actually finished the last book in my traveling stash yesterday. _Virgin Suicides_.” 

“A critique on the emptiness of suburban life? How fitting.”

“I guess that’s what it is. I always thought of Lex’s perspective the most, even though it’s from the point of view of the boys. She wanted so much that she didn’t want anymore.”

She stopped eating, pensive for a moment.

“What did you think of the movie?”

“Doesn’t compare. Nice soundtrack though.”

“Well, it sounds like you need to restock. I vaguely remember from the last time I was here spending hours in a bookstore while my mom attempted to chat up some fisherman.”

“She catch any?”

“Unfortunately yes. She also conveniently lost all their numbers.”

“What a siren.”

The banter flowed eerily well. Strolling together and shooting the shit was so simple and fun, totally unlike the cold awkwardness of last night’s car ride, or even the palpable sexual chemistry from their moment in the parking lot. Jess tried to not wait for the other shoe to drop. 

Rory led them, with a few wrong turns and the help of a local, to the book store. It looked deceptively small on the outside, but was one of those long and narrow ones that had aisles that crept impossibly far back. Tight but easy to lose yourself. And best of all, small town prices. 

They fell into their usual browsing routine. They always shared a deep concentration in a bookstore or a library. Occasionally they’d brush elbows, show each other an especially cool-looking addition or ask for an opinion. 

Rory dragged a pile of books to the front of the shop while Jess kept it a bit more modest. He bought some Henry Miller he had never heard of, _Chelsea Girls by_ Eileen Myles because Sasha told him he would like the observations about New York, and a surprise he hoped Rory wouldn’t notice in her excitement about finding a signed copy of Joan Didion’s _A Book of Common Prayer._ She gushed about it being on discount because there was a soup stain, which she thought just gave it more character.

The cashier, a very old, wormy looking man who probably owned the store, rung them up in silence while Rory rambled about her finds. 

“You know you’re going to have to carry all of those, right? We’re equal opportunists, remember?”

The store owner handed her a recycled paper grocery bag. Rory thanked him and rolled her eyes at Jess, packing away her books. Jess smirked at her, nudging her with his hip and taking over, carrying the bag out of the store. Rory laughed, following him.

“You are one good looking pack mule.”

Rory threaded her arm in his and it was good, almost too good. 

They found a small park that reminded Jess a little too much of Stars Hollow, but it was still nice. They laid out their jackets and slumped onto the grass. 

“Hey, I got something for you.”

Her eyes widened slightly when he pulled out a book. She grabbed it, flipping it over. 

“ _Speedboat_. I’ve never heard of it.”

“It’s from the point of view of this journalist in the sixties, totally non-linear. It’s basically a bunch of observations about how absurd people can be. But it’s compassionate, funny, sparse in that journalistic way. It’s very you.”

She looked up, almost blushing. 

“Thanks Jess.”

They laid in the grass, which was extra warm and verdant in the sun, and read into the afternoon. Jess peeled through Henry Miller. It was too dense but Jess still enjoyed the long and leisurely descriptions of Big Sur. Rory read _Speedboat_ , every once in a while laughing out loud or giving a pensive frown. It seemed every chapter Rory and him were moved a little closer, until the top of Rory’s head met the edge of Jess’ waist–and there they stayed–content. 

Rory gave a little gasp that meant she found a quote worth sharing. Jess looked up. 

“Listen to this, ‘When you are truly stuck, when you have stood still in the same spot for too long, you throw a grenade in exactly the spot you were standing, and you jump, and you pray. ”

Jess rolled it around in his mouth, looking down at her. They both relished in the words. 

“Is that about me or is that about you?”

She felt caught in a good way. 

“Both of us, I guess?”

“Tell me more.”

Rory slid her receipt into her book and let it lay on her chest. She sighed, pulling the words together. She hadn't been hiding it really, how she had been feeling before he showed up. He was bound to ask eventually. He could read her in all the ways she couldn't read him. 

“I think, it’s been harder to know who I am since high school. I know I want the challenge, of being a small fish in a big pond again. It’s just, hard to remember that I want it sometimes. To feel worthy. I don’t know. Adulthood, even though it’s not even as real for me as it is for you, it feels sterilizing sometimes. And lately, I’ve caught myself regressing.”

“Dean?” he asked, thinking of how he was there when Jess came that night. They hadn't acknowledged it until now. 

She looked up, expecting jealousy or for his guard to have gone up. But he just looked inquisitive, gentle even. She bit her lip. 

“Yeah.”

He nodded, deciding not to press. 

“You know I hold you in high esteem…”

“But?”

“You don’t have to be perfect. Becoming an adult isn’t going to look like what sixteen year old Rory thought it was gonna look like. You’re gonna fail, you're gonna go through the motions. You’ll want it again. I’m pretty confident Rory Gilmore loves learning, with or without the expectations she’s held to. And, she’ll _always_ be worthy of the pond in which she swims.”

Rory touched his arm in gratitude, remembering how when he talked it was usually the words she needed to hear.

“Wow. So wise. And so wordy.”

“Don’t get used to it.”

Jess gave her a pat on the head that somehow wasn’t awkward despite their position, and they went back to reading.

He had to ask.

“So, is coming with me you throwing the grenade?”

“Actually, I think I’m doing this so I don’t throw the grenade.”

He smiled at that, crooked and sweet behind his book. 

  
  



	5. Chapter 5

**Summary for the Chapter:**

> Thanks everyone who commented for your kind words! I never expected to write something like this. I haven't even watched the show since I was 14. But it's been surprisingly fun! Anyways, this one's a doozy.

Their day continued in a leisurely, playful manner. Rory was surprised at how much it felt like a vacation. They played stupid arcade games at the pier and ate hot dogs. He still sucked at all of them, and she won him a prize, smugly handing him a pink teddy bear that he pretended to strangle. _The game is rigged!_ The laughter came so easy. 

All of it felt like repeats of moments from their past relationship, but better. 

They eventually wandered closer to the edge of town where they found a tacky Italian restaurant. 

“You know it’s run by real Italian-Americans when there’s a felt painting of bulldogs playing poker.”

“Does that mean the food is going to be good?”

“Absolutely not.”

He was right, the food was over the top and not very good, but she still devoured it. And the balding, thick accented restaurant owner kept yelling into the kitchen in Italian while the waiter, his American son, looked at them embarrassedly. 

“I understand why he’s angry. This ziti sucks,” Jess muttered to her. 

They both spent the meal trying and failing to hold in their laughter at the absurdity of the whole thing, mouths full of pasta and red sauce. 

. . . 

They wandered as the sun started to burn from yellow to pink, Jess' hand often drifting to her elbow or lower back. Not possessive, just disarming and organic little touches. In their post dinner bliss they passed a divey looking bar, and Jess got a mischievous look in his eye–stopping them both. 

Rory stopped, looking in the front window. 

“It looks like–”

“The bar where they shot the pool scene?”

“Jess, how many times have you seen _Mystic Pizza_?”

He shrugged innocently.

“Just the once.”

“Liar!”

“What? Julia Roberts is hot!”

The bar was all enameled wood, dingy chairs, two pool tables near the back. It was still early, so the crowd was sparse and decidedly masculine–men having a drink after their 9 to 5. It did look like the bar from the movie.

“You don’t think it’s actually where they shot it…”

“Whether it is or not, it’ll give you the full tourist experience–the part you couldn’t get when you were twelve.”

She looked skeptically at him.

“But we’re underage!” she hissed. 

“Come on Rory, you really think I don’t have a fake ID?”

“And you think I do?”

“Relax! I’ll order! And divey places like this rarely card anyways.”

She wasn’t totally convinced. But she was feeling spontaneous, and there was something inviting about the bar–in a cinematic sense at the very least. It was warm and classic and totally unpretentious.

She opened the door, holding it for Jess, who laughed at the self-satisfied look on her face. Attempting to be casual but quick, she went for the table farthest from the bar. He touched her elbow to stop her, still looking devious. 

“Have you ever had a boilermaker?”

“No. Would I like it?”

“Probably not. But it’s definitely something Julia Roberts’s character would drink.”

“What is it?”

“A beer and a shot of whiskey.”

Not her drink of choice, but it felt fitting. Grown up in that rough-and-tumble way. It was very Jess. 

“Gross. Now go get us some. I want the full experience.”

“As you wish.”

Jess went to the bar while Rory sat at a corner table. He looked back at her. She looked out of place in the dingy bar, but also not. He always saw the dangerous side of her–the risk taker. The one who wanted to report from warzones and kissed with a hunger. 

He brought back the drinks on a tray and they fell into that easy banter, warm with booze and the anonymous clammer of the bar. 

. . .

“Do you have a favorite birthday memory?”

He tilted his head, remembering not his own birthday, but one of Liz’s. The song on the jukebox provoked it– _I’ve got a brand new pair of rollerskates you got a brand new key…_

“What are you thinking?” Rory asked, taking a sip from her beer. He had a little smile on his face, eyes downcast. 

“Oh nothin’. Just someone else’s birthday. Funny story,” he brushed it off, leaning back in his char.

“You have to tell me now!”

He looked good like this, relaxed. Like a cat in the sun, a quiet confidence. She even liked his hair. It wasn’t trying to be anything–just soft and tucked behind his ears. 

“It’s not _that_ funny.”

“I just gave ten minutes of airtime to a story about Luke decorating a Spice Girls birthday cake. Your inherent pithiness will make anything you say interesting at this point.”

He huffed a laugh.

“Okay.”

“Yes!” Rory pumped her fist in victory. Maybe she was a little buzzed. 

He can’t believe this even came to mind. He hadn’t told anyone this story. Hell, he hadn’t told anyone much of anything about his life. 

“It was Liz’s birthday. I was ten. She wanted to go rollerskating in Central Park, just me and her.”

Rory’s eyes widened in surprise, not expecting his mother to be a part of the story, much less in _roller skates._

“Oh my god, the image of you on roller skates. Divine!”

He shook his head, she kinda sounded like her mom when she drank. He didn't mind, it just made him smirk.

“I know, I know. I was mortified by the mere thought, but I was ten and vulnerable to persuasion. So we took the subway, rented some skates from this little spot by the park. I was awful. Apparently she had made the time to learn ‘cause she was pretty good. Anyways, it turns out, every Saturday this crew of dorks goes to the park to do _roller disco,_ ” he said the last words with disgust. 

Rory burst out into uncontrollable giggles. 

“Just wait, it gets worse. Two old ladies in fucking shiny leotards take a liking to me, and Liz being a sadist and all, pushes me toward them. I was a pretty small kid, so it wasn’t hard for these old bags to try and make me dance with them. Meanwhile, I’m just trying not to fall!”

Rory was in stitches, her gut cramping as she dissolved into hysterical laughter. 

“My mom was just dying laughing while I was being tortured by the cast of _Xanadu_ , and here’s the kicker–she laughed so hard she pissed herself.”

“What?!” Rory practically yelled, getting looks and even chuckles from nearby tables. 

“Yeah, she’s rolling backwards, laughing like a maniac, literal urine running down her leg. I had to give my incontinent mother my jacket to tie around her waist on the subway ride home.”

“Stop! You have to stop! It hurts!”

He watched her recover, feeling warm at the sight of her doubled over. She sighed, wiping tears from her face.

“God you undersold that story. Wow.”

“Yeah, it was a good day.”

Rory gave him a sweet look then, registering that Jess talking about his childhood, much less his mom was a rare occurrence. 

“Thank you,” she said in earnest.

“Geez. You don’t have to get all sappy on me.”

Jess felt exposed all of a sudden, hiding behind his now empty pint glass. The shot had loosened him up more than he expected. But he knew it was mostly Rory, how she made him feel safe. 

“Hey, want another beer?” Rory asked, diffusing the moment. The sentence felt so foreign in her mouth. 

“Yeah, make it another boilermaker. You really gonna order? Not afraid of being locked up in a drunk tank?"

“They didn’t card you! Didn’t you say yourself, no one cares in a dive?” she hissed under her breath, eyeing the bartender. 

“Hey, by all means.” he conceded, gesturing towards the bar.

She got up to go to the bar, the silence of her absence slowly morphed into a regret at bringing up the memory. It came up on him quick, without him realizing. If he dredged up something good something bad usually came with it. The rest Liz’s birthday–the dark and mean part–manifested in his brain. 

She had gone out with her boyfriend to celebrate. When they got back, Liz was so quiet, her arm gripped in his. His face was pale and sweaty and strung out. Jess came out of his room against his better instincts, saw the blood on her lip, and ran toward her–he must’ve known how stupid that was, that he would never win. But that was his _mom_. He was yelling–angry and righteous. 

Her boyfriend wouldn't let go and Liz was begging him, begging Jess to just _stop._ He bit down on the man’s arm and then he was flying _–_ Jess clenched his fists to stop the memory. He couldn’t stop it from coming, the image of the next morning. Of eating cereal like it didn’t hurt to lift his arm, Liz babbling about nothing. _God, just stop._ Jess shook his head, took a drink–only to find his empty glass. 

Rory caught him zoned out as she came back with the second round. He pulled his drinks in front of him, taking a gulp of the fresh beer. There was something grim about his mouth. He looked tired. She was reminded of the days where he would withdraw, quiet and distracted. She would ask but he would never answer. So she stopped asking. 

“Hey, you okay?”

“Yeah.”

He cursed himself, why couldn’t he just be _easy_ for one day? Why did he have to swing from content to miserable?

“Jess.”

“Rory.”

“I can tell something’s off–”

He tried to be gentle but it still came off harsh.

“Leave it. I was just distracted.”

She let him off the hook, opting to try and cheer him up rather than pry.

“So was the bartender apparently, because she didn’t card me either. God my heart was beating so fast. It was harder than I thought.”

“Breaking the rules?” 

He kept his voice light, trying to come back from his shitty memory. He wasn’t totally succeeding. 

“Hey, I break the rules!” 

“What is that?” he asked, pointing at her drink. It was pink. There was a cherry.

She looked embarrassed. 

“Shirley Temple,” she admitted sheepishly.

“You’ve got to be kidding me–”

They were interrupted by a burly, bearded looking man in a camo baseball cap tapping on Rory’s shoulder. Jess' face quickly went from melancholic to cold and hostile. Rory turned to look. He had a smarmy smile on his face poorly concealed by faux-sheepishness. 

“Hi, I saw you at the bar and I had to come over. You are about the prettiest girl I have ever seen.”

Rory thanked him, looking uncomfortable. She turned away from him but he lingered, looking back at his friends who jeered him on. 

“Hey, why don’t you go breath down someone else's neck? Or better yet, buy an inflatable doll.” Jess snapped. 

“You got a problem buddy?’

" _You got a problem buddy_...what a fucking cliche,” Jess muttered. 

Rory felt the moment escalating, the man behind her not taking well to Jess’ antagonisms. 

“Jess, enough with the machismo, I’ve got this.”

She turned to the man. Jess’s jaw clicked. The tension he had been tried to alleviate in his muscles came back with a vengeance, the anger he had felt the night of Liz’s birthday flowing back into his body like a shockwave. 

“Thank you, but I’m not interested. It would be wise for you to go back to the bar," she said, cold and formal.

His demeanor changed. He wasn't trying to get her number anymore, now he obviously wanted to start something.

“Oh don’t let this twerp stop you from having a drink with me. I saw how you were sticking your little ass out at the bar. I know the signals,” the man said in an arrogant lilt. He leaned over her. 

“If you don’t want a Shirley Temple in the face, I suggest you step back–” 

But it was too late. Jess was already standing, looking hard and dangerous. A live wire.

“Jess sit down!”

“Oh what, you wanna fight me?” he sneered, looking back at his friends. “What do you think, should I cream the scrawny-son-of-a-bitch?"

In an eruption of blind rage Jess leapt at him, his fist meeting hairy cheek. They tumbled through and out of the bar, knocking over a table–glasses crashing to the floor. The bartender yelled profanities as they tore at each other. Rory chased them, yelling for them to stop. Jess was fighting like he had nothing to lose, landing solid hits. But it was like a street cat fighting a pit bull, and he was never gonna win.

Out on the sidewalk, the man finally got Jess on his back, ready to kick him in the ribs when Rory pushed her way in front of him. 

“Stop! Just stop!” she demanded, voice ragged. 

The man looked at her for a moment, looked down at Jess with a curled lip, before cursing some incoherent insult and walking away. His pack followed him, snickering. 

Rory looked down at Jess, feeling helpless and angry. She caught a glance of blood on his face before he turned away–getting up and storming across the street. 

“What the hell was that? Get back here!” she yelled after him.

He wouldn’t listen.

She yelled his name, feeling so stupid. He was curled into himself, walking towards the pier. All she could do was follow. 

. . .

Eventually she caught up to him where he was sitting on a bench–hunched and scowling, Rory tried to peek at his scrapes. Her breath was still coming out shaky. She felt like they had taken five steps back. Fighting like that was something she thought he had left behind in high school. She was mad at herself, for being deluded into thinking Jess was softer, more reflective. 

“Why did you pick a fight with him? He was twice your size,” her voice was cold but still quavered. 

“Cause he was a fucking asshole,” he hissed, not looking at her.

“So? I don’t need you to defend my honor. I can protect it just fine on my own.”

“It wasn’t a conscious decision Rory, it just happened,” he bit. 

“Well then your subconscious is dangerous! The only reason he stopped is ‘cause I leapt in front of him.”

“I could have handled it.”

He felt a twinge of guilt, she could’ve been hurt. 

“You’re not a big man Jess.”

“I’m scrappy.”

Rory sighed, not getting anywhere. 

“Are we going to talk about this or just repeat that night at the party?”

Jess looked up from his lap, the angry red bruise on his cheek and the scrape on his chin in full relief. There was still a residual violence in his eyes, not at her, maybe at himself. 

“I didn’t start that one”

“No, but you wanted to. You were waiting for the chance to fight Dean the whole time,” she said, low and bitter. 

Jess wanted to argue but couldn't. His mouth twisted. Rory tried to quell her anger, sitting next to him with a sigh. 

“Look, I don’t want to dwell on the past. I just want to know why you’re so...self destructive.”

Jess looked back down at his lap.

“I don’t see it that way. The fighting at least.”

Rory went silent, hoping he’d elaborate. Maybe it was the booze, or the adrenaline, or maybe it was Rory looking at him like this was his last chance. Either way, he felt it building up, his lips loosening–throat burning. 

“What happens if I turn the other cheek? Who am I then? And don’t give me any ‘high road’ bullshit. You know that’s not me.”

She held back, hoping for more. Instead she got a tired sigh and more silence. 

If he didn’t stop himself now he wouldn’t stop. Why did she want to know anyway? What did it matter? The dark part of him was always going to be there. He didn’t know any other way to be. 

“I don’t have to tell you everything. You don’t want to hear everything,” he muttered. 

“Yes, I do. That’s kind of the point of this, coming with you.”

Anger crept up in him, acrid on his tongue. He couldn’t believe they were here again, repeating this argument. But he knew the stakes were higher this time. 

“Well it isn’t for me. I’m here because you make me happy, not for some botched therapy session.”

Rory threw up her hands. He was being impossible.

“Just tell me something real, Jess! Is that too much to ask? After everything?”

“That _is_ real!”

He always told her what was real, even the silence–it was always real. 

“About you!”

What could he say to her? He barely could confront himself. 

“Watch a D.A.R.E PSA! You’ll probably get the same idea.”

“What does that mean?!”

“That my existence is a cautionary tale!” he yelled, unbridled now. 

She had done it, found the chink in his armor. And she was regretting it, balking at the self-loathing in his words. He looked away from her, jaw locked, out onto the water. She could only see half of his face. His eyes gleamed. He started to speak, his tone quick and bracing. 

“Liz had me at sixteen, but she was no Lorelai. She was messy and selfish and not evil, but...not ready. Drug dependent. Sex dependent. I came around and she loved me, but she was scared of me too. So she laughed a lot and drowned out the fear, and barely managed on food stamps–still laughing. And then there's my deadbeat dad running as fast as he could. He was scared of me too. He would be easy to hate if he wasn’t so... _nice._ Not present, not strong, but nice.”

He looked angry at his own words, He hated how easy it was to finally say it, like his mouth was betraying his body. His throat convulsed. 

“And of course all of the boyfriends, the fucking vampires, sucking the money and the life out of Liz and out of me. They hated me. Some of them really, really hated me and they showed it. So yeah. I fought. I threw whatever punches I could, cause I was fucking angry. I’m still angry. Cause then there’s me. The fucked up byproduct of it all. And you're sitting here looking at me...like you're scared of me too.”

His voice broke at the end, tired. Done. 

There were tears rolling down Rory’s cheeks now, hot and sticky. He turned to her, the full view of his crooked-mouthed grief too much to bear. 

“Is that what you want to hear? Is that what you came here for?”

His voice was raspy now, worn out. She couldn’t say anything. Because yes, that was what she was here for. But how could she say that out loud? How cruel would that sound? So she cried silently instead. 

He pulled out his pack with frantic hands, putting a cigarette between his lips. He flicked at his lighter, cursing, unable to get a flame. She watched him struggle, his fingers unable to get enough purchase. She realized his hands were shaking. 

Wiping her face on her jacket sleeve, she got up and put her hand over his–wordlessly taking the lighter. She lit his cigarette and he looked at her with a sort of reverence, a questioning, so different from his harsh anger. It was intimate as he pulled in smoke, letting it wisp out of the corner of his mouth and away from her face. She slipped the lighter into his pocket. 

“Just...what makes me different from them?” he whispered.

He gave her this look that begged, _please, tell me I’m better,_ and she was choking on her words. 

“Because–because you have a choice. To be stronger.”

It sounded thin as it came out. It wasn’t enough, but it was honest, and she didn’t know how to make him believe. He nodded, looking exhausted but not entirely convinced. 

“And you’re good,” she added. 

He looked up, eyes suspicious.

“You have to trust that I know. You’re _good_ Jess. When you’re not having a cat fight with some idiot duck hunter.”

He didn’t laugh, but he looked a little less tortured. He dropped his cigarette and stepped on it, looking up at her with a tender gratitude that made her breath catch. 

“Okay.”

  
  



	6. Chapter 6

**Notes for the Chapter:**

> Dirty!

Back in the hotel room Jess sat on the toilet seat while Rory brushed an antiseptic wipe across his cheek. He had grumbled about her mother henning when she asked for a first aid kit at the front desk. _Jess, if you think there’s a world where I kiss you with an infected wound on your face, you’re delusional._ So Rory stood over him in the weak fluorescents of the bathroom while the alarm clock radio gave off a tinny rendition of ‘Magic Man’ by Heart. 

“Give me your hand,” Rory said in a gentle command, tearing open another antiseptic wipe. 

Jess offered it to her, a couple of the knuckles slightly split. Rory absentmindedly stroked the inside of his wrist. He always had nice hands, tinkering hands, hands that would cradle the back of her neck or the dip of her waist with a strength– 

“Rory?” Jess asked, as she had been standing there dazed–the wipe still unused.

She shook her head slightly.

“Right.”

She brought his hand closer, cleaning off the specks of dried blood between his knuckles. 

Jess looked up at her, feeling a warmth overtake him. There was something peaceful about the moment, despite the hiss of pain whenever the rubbing alcohol hit a scrape. As much as he hadn’t wanted to at the pier, he finally said aloud what had been festering in him for years. It was still in him, but for the moment he was buzzing with an unlikely relaxation. 

He hadn’t needed her to give him first aid–had managed plenty of times without it–but it obviously gave her a sense of control. And maybe it felt good to give in a little, to let her care for him–even if he pretended it was all for her sake. He hadn’t been observed so closely like this before. His face cradled in her hand, totally still. His hand in hers, malleable. She was taking more time than she had to, her brow furrowed and her hair tucked behind her ears. She looked strong.

Rory looked up and caught his eye. He had an inscrutable look on his face. 

“What?”

“Oh nothing,” he evaded, coy. 

“You must know how annoying that is!” 

He looked up at her with an ironic reverence, almost laughing. His scrapes looked smaller with the blood wiped off. His hair was all pushed back, still ungelled but not totally unlike when she first met him. 

“There’s just, something uh, kinda sexy about this.”

Rory barked out a surprised laugh. 

“What do you mean?”

“I dunno, motel bathroom, Heart playing in the background, you cleaning my battle wounds,” he joked. 

“Oh shut up.”

Rory started to release his hand but he kept it there, clasping their fingers. His smile was still coy, but genuine. All of the stark, rakish beauty of his face was as clear as ever in the shitty motel light fixture. And he was looking up at her like he was recording the intricacies of her face. His worn, black Wrangler button up had a little hole in the chest, and she felt the childish but also very adult urge to hook her finger in the hole. Obviously he could read it in her face because the hand that wasn’t holding hers reached to clutch the edge of her t-shirt. But she still stood above him, she still had control. He wanted her to be in control. 

“I was going to waste it,” it rushed out of her mouth before she knew what she was saying. 

He raised his eyebrows.

“Waste what?”

She almost stammered now, but forced herself to be bold. 

“My virginity.”

He gave her a fond, if a little confused, look. 

God why was she saying this? Why did she have to bring up Dean of all people?

“I was–He came back into my life–I felt like I should but–”

He nodded solemnly in understanding. 

“It’s alright, I get it.”

They sat there, hands still clasped. 

“But now,” she started. 

Jess looked up. The heat between them solidified. It gained explicit meaning. 

“It’s everything people say it shouldn’t be. You look like Petey the dog, and we’re in a sleazy motel with double beds,”

“Rory, you don’t have to sleep with me just cause it seems like unfinished business.”

It was firm how he said it. But he had misunderstood her. She couldn’t help a laugh.

“No. That’s not it.”

 _No more talking_ , she decided, sliding her hands slowly into his hair. It tousled easily in her grip, becoming unwieldy. She brought her hands around his jaw, careful of the tender spots. His eyes darkened, the hand gripping her shirt sliding onto her bare waist, down into her back pocket. She dove in for a kiss and that was it. Different from both the kisses they shared in Mystic, this wasn’t an offering or a taking. It was just heat. He pulled her onto him where he sat, hands sliding under the band of her bra. 

She wasn’t nervous or unsure. Everything about his touch said _I want you_. And there was nothing condescending about it either. He wasn’t overly careful and he didn’t take the lead. He just kissed her in that quiet and ferocious way he always did, tongue dipping into her clavicle. She unbuttoned his shirt, grateful they were snaps. His wiry frame smelled a little like smoke, a little like a cat laying in the sun, something salty and warm. 

He took off his watch, tossing it in the sink before standing.

“Bed?” he asked, breathy.

She hooked a finger into one of his belt loops. 

“Bed.”

He fell back onto the mattress, pulling her on top of him. It felt right to stay for a moment, breathing into his chest. His arms came around her waist. In the stillness something struck her. She looked at him, chin resting at the divot in the center of his chest.

“I’m not taking advantage of you while you're vulnerable, am I?”

“What?” he asked incredulously. 

“Well, you’re bruised, and all that at the pier,” she referenced carefully. 

He looked at her, thoughtful, but in the end huffed a laugh. 

“If that was your plan all along you’re a diabolical genius."

“I’m being serious!”

He ran a hand through her hair, lingering at the ends. 

“I wouldn’t qualify this situation as you taking advantage of me.”

He looked hungry then. She flipped onto her back and he followed, hovering over her. She lifted her arms over her head and he lifted off her shirt. 

“Need help with the bra?”

“No,” he deadpanned with a playful smirk. 

And maybe she was a little nervous now, as he was pressed against her, hands fiddling at the clasp on her back. It came free and he let her pull the bra over her shoulders, tossing it to the carpet. He looked at her with soft, half lidded eyes. 

“How experienced are you?” she blurted.

Again it came out before she could stop herself. He sighed, rolling onto his back next to her. She tried to bring her hands casually over her chest.

“Do you really want to know that right now?” 

“Kinda.”

He perceived the twinge of insecurity in her eyes. There was no way a summary of his escapades would wipe that away. He turned to her seriously.

“Rory, there’s no comparing.”

“Why? What was wrong with them?”

 _Or with me_ , she couldn’t help thinking, even if she knew it was ridiculous. 

He sighed again at her stubbornness. He tried to remember if he could’ve used some reassuring words his first time, instead of a chaste pat on the ass and a _see ya_. But that was different, it was casual.

“Nothing. But I didn’t love them.”

She blushed.

“Oh, right.”

“So have we covered all our bases? Or do you want to call your mom real quick?” he quipped. She slapped his arm.

“In all seriousness, do you have a condom?”

He pulled his wallet from his jeans, digging around until he found a Trojan, holding it up for her to see before setting it on the bedside table

“Wow, you _are_ a hoe!”

He shut her up with a kiss, hands sliding over her breasts. She reached down to unbuckle his belt. They shucked off eachother’s pants, laughing. 

He sucked her nipples, mouthed her belly, kissed her thighs, and it was real. It wasn’t contained in lingering fervent looks. She was actually bucking against him and it was scary as it was natural.

He took her in, how lithe she was. A body like a river. He looked up at her from in between her legs, hands at the hem of her underwear. She nodded, breathing heavy, and he pulled them off with a smile to tell her there was no way he wouldn’t like what he saw. He pulled her legs over his shoulders and knelt in front of her, not taking off his briefs like she thought he would. 

“Oh!”

He looked up at her again with a look that was pure, impish sin. 

“Don’t worry, I’m good at it.”

And before she could roll her eyes he was licking, and all she could do was give an exhilarated laugh because he was good at it. Of course he was. 

  
  



	7. Chapter 7

**Notes for the Chapter:**

> Kind of a stepping stone chapter.

Jess had his head right below her chest, almost dozing off while she half watched a History Channel program about the Cold War. She was wired, the idea of _virginity_ circling in her mind. Did she feel different? Not really. There was a slight heaviness in her gut, akin to guilt. Is this what the town princess would do? Absolutely not. But above all else she felt satisfied, languishing naked with a very loose and sleepy Jess. It didn’t go away though. The little twinge. 

“How did you lose your virginity?” 

Jess hummed a protest into her belly.

“Too many questions,” he grumbled. 

Maybe she was a little heavy on the interrogation tonight. She scratched his head, absolving him of answering. After a moment though he moved onto his back, looking up at her. 

“Jenny Abelman. I was in ninth grade, she was a year older which felt like a big deal at the time.”

She wasn’t surprised, but couldn’t help but compare herself to the theoretical brood of women he would have slept with between then and now. 

“Ninth grade huh?”

“Don’t get the wrong idea, we were both dorks. I was shorter than I am now and could barely hold a conversation. She was the class clown, had a whole Gilda Radner thing going. I caught her eye at some party and we had sex in the bathroom. Very unceremonious.”

“The bad boy and the class clown. That’s cute.”

Her tone was light, but he still noticed a pensiveness in her face.

“Yeah. Maybe.”

Of his encounters Jenny was the closest he got to cute. When he had sex for the first time he didn’t give it too much thought. It just became a new way to feel good. But Rory was a chronic overthinker. And he knew it was more complicated for women. Sex was more political. 

“What’s on your mind?” he asked, despite wanting to just fall asleep on her belly. 

“Oh I dunno. I feel good. A little guilty too I guess.”

His brow furrowed. 

“Why guilty?”

She couldn’t explain it. It was something to do with her role in the world, her family, her town. Who she was supposed to be versus what she wanted. 

“It’s just a feeling.”

He nodded, accepting there were things he couldn’t understand. 

“I have a Grace Jones album in my car. Maybe her sexual empowerment will rub off on you.” he deadpanned. 

She laughed one of those surprised, contagious laughs. 

“I’m empowered! Maybe not Grace Jones empowered,” she trailed off. 

He hummed in response, burying his face in her waist. She felt the tickle of his hair, the roughness of his scrapes and a little stubble. Her eyes felt heavy. Finally wordless, she turned off the tv and the bedside lamp and slipped into his arms. In minutes her head was clear. Soon after they both slept. 

. . . 

Jess woke up early the next morning with his forehead pressed against Rory’s back. The ends of her hair just brushed the top of his forehead. Her ribs rose and fell softly with her breath. 

It occurred to him that he had never woken up like this, wrapped up in another person. It was nice. Then again, he couldn't imagine so content and trusting with anyone else, not even himself. Then it struck him, _Rory has to move out of Yale tonight._ He nuzzled his head into her back, trying to drown out the flicker of foreboding. Now that he had it, what if he lost it? He slid out of bed and padded into the bathroom for a shower, trying and failing not to think about what came next. What reality looked like beyond this weekend was starting to loom. That was always the hard part for them, functioning in the real world. 

He rubbed the grime off his face, letting the hot water and soap sting his scrapes. He would clear his head, get dressed, get her coffee, and not ruin it. It was a risk. How far could they get before the spontaneity and affection couldn’t cover for the fact that he was kind of a fuck up? This trip had been a crash course in whatever communication bullshit he read about in Luke’s self help books. But was it enough? He turned off the hot water, letting a cold spray break his train of thought. It was too early for this. 

He left a note on his pillow that read ‘COFFEE RUN’. He spent too long debating whether to add a heart, before realizing what a corny idiot he was being. With any luck she would sleep for a while and he would be there when she woke up. He took one last glance at her, cheek pressed into the pillow, her mouth hanging open a little bit. No matter what happened it was worth it to see her like this. Her lashes cast soft shadows on her face. A lock of her hair sat above her upper lip like a mustache. He took a mental picture, on the off chance that this was the last time he’d get to, and silently slipped out of the room. 

. . .

Rory woke lazily, stretching everything. There was a gentle ache in her muscles. The scratchy old bedding felt like it could swallow her up, like she could sleep all day. She patted the space next to her, no Jess. No sound in the bathroom. Eventually her hand met paper. ‘COFFEE RUN’. She had to applaud his economy of language. 

She had been dreaming about that trip she took with her mom, a day where they had driven out of Mystic to a secret cove. In the dream they wore big stripey old-fashioned bathing costumes, and shared a whole turkey. But that wasn’t important. She remembers the actual, non-dream day. Diving into the waves, floating on her back, her mom watching her from the beach in a big ridiculous hat. 

She knew intellectually that she had to go back to Yale that night to move out her stuff. But she wanted to dwell in the anonymous escape of Mystic a while longer. She couldn't think of what tomorrow looked like, especially before coffee. With epic timing, the door clicked open and in came Jess with two togo cups. 

He sat on the bed, handing her her coffee, putting his on the bedside table. The acrid smell of smoke floated off him.

“You smell like cigarettes.”

“There’s a reason they call it a habit.”

She didn’t press and took a sip of her coffee. 

“This is still hot. Did you run back here or something?”

“I’m a fast walker.”

He reached into his big jacket pocket and dropped a white paper pastry bag on the sheet next to her. 

“Ugh! Angel!” 

She immediately tore into the danish while he watched her, smirking. The farther she got into her coffee the more conscious she was that while he was fully dressed–leather jacket and all–she only had the bedsheet. 

“I’m still naked,” she noted, mouth full. 

Jess’ smirk widened, eyes laughing. 

“That you are.”

In what felt like a departure from her virginal self, she didn't really care that she was naked. She finished her danish, sipping at the last of her coffee, thinking of the secret cove.

“I know what I want to do today.”

  
  



	8. Chapter 8

Jess drove along the coast while Rory looked for a familiar landmark, anything that reminded her where the cove was. Her mom had only been there once before with her father, and she had found it. She was completing the circle in a way, bringing Jess there. 

“So we’re going to a beach from your dream?” Jess asked skeptically. 

She turned down the stereo, which blared Bad Religion. Jess’ choice of course. 

“Yes, but I’ve actually been there!” she insisted, scouring the roadside.

“Whatever you say.”

They kept driving, Jess looking more skeptical by the minute, but mostly just enjoying riling her up. She ignored him, racking her memory for how long she and her mom had driven from town, whether it was a dirt road or a parking lot. 

“All I’m saying is that the guy at the motel lobby had no idea what you were talking about,” Jess jibed.

“Pipe down buzzkill!” she shot back, her tone light. 

“Yes mamn.”

Then she saw a speck, getting bigger as they drove. It was a piece of driftwood mounted to a tree. She flashed back to how her mom had excitedly gasped at the same piece of driftwood, swerving off the road. 

“There!”

Rory pointed and Jess pulled onto the side of the road, turning off the ignition. She gave him a self-satisfied look, creaking open the car door. 

“Incredible,” he muttered sarcastically, marveling at her luck. 

Between the car and the shore was a thicket of canopy and oak trees, the ground below a carpet of gnarly shrubs. He could hear the ocean through it all, a dim hiss. Rory excitedly wandered along the edge of the road, looking for a trail. 

“I never struck you as a lover of nature.”

Jess locked the car, grabbed the paper bag full of lunch from the deli, and walked up behind her. He peered over her shoulder at the impenetrable greenery.

“I’m not, I’m a lover of the beach. Me and my mom go to a new beach town every summer, and I’ve always been kind of a natural swimmer.”

“Well you’re a natural everything,” Jess said with a naughty lilt in his voice.

When Rory understood she shoved him a little, flattered but trying not to show it. She kept eyeing the treeline, looking for a trail. Then she saw it, just out of sight behind an oak was an impossibly narrow dirt path. She grabbed his hand and led him. 

They pushed on through the thicket, Rory getting more excited as the smell of the Atlantic became stronger. 

“You’ll have to check me for ticks,” Jess complained.

“Happily,” she quipped, pushing away a tree branch to reveal  _ it.  _

The crystal clear cove from her childhood. Driftwood piled on the beach, a whale pelvis sticking out of the sand, the water crashing to shore in big piles of foam. 

“I told you!”

“You sure did.”

Rory kicked off her shoes, Jess dropping the paper bag. He actually felt kind of...moved. He realized he hadn’t encountered nature that was so untouched before. As far as he was concerned Venice Beach was a cesspool, and he never dared to go with Luke on his fishing trips. He had never been camping, or on a ‘hike’–whatever that was. He was still a city boy through and through and he still hated sand. But this beach felt like it must have been superimposed onto the earth from Rory’s dream. It was otherworldly. And Rory on the beach, silhouetted by the cold and clear blue of the water, jeans rolled up her calves, hair askew in the wind, it was enough to make a man sentimental. 

She turned around, seeing Jess standing right where she left him. 

“Come on!” she called through the wind. 

He untied his boots and stood at the very edge of the water. She was up to her knees, hiking up her jeans as far as they would go. 

“If you're gonna get your pants wet you might as well go all the way.”

Rory looked back at him, devious. She ran back to shore in big splashing steps, and started stripping down to her underwear. 

“Rory I wasn’t serious, it’s freezing!”

“It’s officially spring, it's not that cold. Do it with me!”

Jess could see her skin prick and blush at the cold as she stripped, tossing her clothes onto dry sand.

“Hell no.”

“Come on! Since when am I the more spontaneous one?”

“I’m not a good swimmer!”

Rory had a big young grin on her face. 

“I'm CPR certified”

He wordlessly took off his jacket, throwing it to the sand with faux indignance. Rory gave a loud giddy laugh, running further into the water and screeching at the cold. Deciding to just get it over with, he dove into the backwash. 

“Fuck it’s cold!”

He swam out to where she stood in chest deep water, grabbing her by the waist and holding her tight.

“You’re the only warm thing.”

She grabbed his hand, deriving more meaning out of what he said than he intended to give. A small wave crashed over them–breaking their embrace. They swam to shore. 

They stripped off their underwear and tried to warm up in their dry sandy clothes, Rory sat between Jess’s legs eating her sandwich. They both shivered a little, but it wasn't a wholly uncomfortable type of cold. It was tingly. And she felt cozy in his arms. Unconsciously she wiped her runny nose on his jacket sleeve.

“Gilmore! Gross!”

“Sorry!” 

He leaned over her shoulder and took a big bite of her sandwich. 

“So, do you like the beach now?”

“No. I like this beach,” he answered, chewing. 

“What did you even do in LA if you don’t like the beach?”

She craned her neck to look at him. He rolled his eyes at the question. 

“Work. Read. Walk.”

“Oh you’re no fun.”

“Well it wasn’t very fun.”

She wrapped up her sandwich and put it back in the bag. 

“Well what about New York?”

He sighed. 

“It’s no carnival.”

“I don’t believe that your day to day life is totally devoid of fun.”

_ Only the kind of fun that makes me feel like shit in the morning.  _

“Can we talk about something else? Or just, sit?” Jess pleaded, not wanting to have another melodramatic conversation about his bullshit.

She registered, leaning back into him. 

“Okay.”

They stared out onto the churning water, bodies thrumming with the calm that comes after swimming in ice cold water. Jess felt at peace, brushing his lips against her temple. He felt happy. 

  
  



	9. Chapter 9

Eventually it got too windy, and they had to unfurl and make their way back to the car. While the beach was cast in a clear purple, the trees were dark. They traced their way around the bends of the narrow trail in silence, out of their haven, into the real world–where they had to face tomorrow. 

Jess didn’t want to ask. He didn’t have any answers. He just knew he didn’t want this to stop, was afraid of what would happen if it did. What would his life look like without her? So he didn’t ask. 

Jess wordlessly took them back to Hartford. The sky darkened, but Jess could still see the outline of her hair, a little wavy from her swim. If he glanced over he could see the silhouette of her face too, the way the ebbing light of dusk made her skin look like velvet. He pushed it down, the answer he expected. He could hear it so clearly, that this was a one time thing. That it would never work in the real world. But they weren't in the real world yet. 

“You wanna put on some music? There’s a box of tapes in the back.”

Rory reached around, grabbing the box. 

“I can’t read the album names.”

“There’s a flashlight in the glove compartment.”

She rustled through the box. There was Bad Religion of course, Xray-Spex, Radiohead, Death, Gil Scott Heron and some hardcore bands she didn’t know. Metallica, but she hoped that and his t-shirt were ironic. And then there were mixes that he had put together. Some of them had the name of states, book titles, or were mixes of his favorite songs from certain bands. It was a well curated box of tapes. Not that she was surprised. That is until she pulled out a tape labelled with purple sharpie. 

“Is this a Prince mix?”

“Yeah.”

“You never cease to surprise me.”

Rory shook her head, trying to imagine all those times in high school she had seen him drive through town with a scowl on his face, that he might have been listening to Prince.

“What? He’s a crowd favorite.”

“This has his cover of ‘A Case of You’ on it. Did you know Joni Mitchell wrote that song about Leonard Cohen?”

“Prince on Joni on Leonard. Now that’s a sexy game of fuck marry kill,” Jess said with a trademark smirk and cocked brow–so naughty she could see it in the dark. 

“What’s your answer?”

Jess pursed his lips, thinking. 

“Fuck Prince, Marry Joni, and kill Leonard.”

“Aw, killing the rebel poet?”

“Don’t you think Leonard’s a little butch for me?” 

“Well you and Joni are meant for each other, given she’s a chain smoker and all.”

“I am not a chain smoker!”

“You had a cigarette for breakfast this morning!” 

He had no answer for that. She kept the game going, humming while she thought.

“My answer is eff Prince–”

“‘Eff’? Does your daily speech abide by the Hays Code?”

Rory rolled her eyes.

" _ Fuck  _ Prince, kill Joni, marry Leonard.”

Jess grinned, nodding approval at her profanity. 

“Marry Leonard huh? Don’t you know he couldn’t stay in one place?”

Rory gave him a meaningful look, tone still playful.

“Have you ever known me to pick the easy thing?”

He didn’t turn towards her, but after a moment took one hand off the wheel, taking hers and squeezing. 

“I guess not.”

She thought of what the easy choice would be in their situation. Going back to her old life, pretending this never happened? No. That would be impossible. Stay with him in New York for the summer, fall into whatever half stable life he’s built for himself? That couldn’t go well, from what little she knew of his lifestyle. She thought the easy thing might be feigning a relationship. Visiting each other, flirty phone calls, the rush of seeing each other only a few days a week. Every weekend would be like Mystic–a rare and idyllic intermezzo where they escaped their regular lives. 

But she didn’t want to be an escape. And she didn’t want him to be an escape for her. She needed to find purpose again, a purpose she had felt herself losing these days. And Jess needed to find a lot within himself. In highschool Rory always perceived Jess to be brooding, flighty, angry–victim to all the adolescent angst one teenage boy could muster. But now she could see in him what was always there. That under all of the love and pleasure and playfulness that he gave her, he was unhappy. 

She knew what they had to do, what she would have to tell him, and it wouldn’t be easy. Rory sagged in her seat, feeling depleted but not without hope. She squeezed his hand.

Rory pulled a tape out of the box, the title of the mix catching her eye. It was her birthday. Jess noticed, taking a breath like he was going to comment on it but didn’t. She slid it in, ‘Coney Island Baby’ by Lou Reed playing. Lou’s voice drifted purple like the sky did, a blur on either side of the car. She opened her window and closed her eyes, feeling Jess’ hand brush her wrist, evening washing over her. She watched Jess mouth Lou's words, his face a blue ghost in the last light of dusk.  


. . . 

They carried boxes down to Rory’s prius, somehow managing to fit all of her belongings in the car with the back seats pushed down. They did so in relative silence, their only communication being a hand brushed against a lower back or hip to navigate around each other. They both knew the decision was in her hands. All his cards were on the table. 

Rory ached at what she knew she had to say, ached at the melancholy look in his eye, at the gentle little brushes against to her hip when he had to pass her in the hallway, at how the sleeves of his t-shirt tightened around his arms and how a little sweat made the hair at his temples shiny. She ached, and she racked her brain for a way to say it so he wouldn’t retreat. So they moved in silence, until everything was packed away and the trunk was slammed. Then all they could do was look at each other. 

Jess waited. Rory shifted from foot to foot. 

“Thanks for helping me with my stuff.”

“Of course.”

“All that lifting at Walmart really payed off I guess. Well that was a fork-lift so I guess you didn’t really–”

“Rory.”

“But I’m sure you lifted boxes with uh, your arms too–

“Rory!”

Rory sighed, already feeling tears crop in her eyes. 

“I-”

“Rory what?”

Jess looked nervous now. 

“I think I have to do the hard thing,” she started, bringing her hand to his cheek. 

His brow was a dark question. She gave a shaky sigh.

“You have to learn how to be happy without me.”

His head jerked back. Her hand fell. 

“What does that mean?” he snapped. 

It wasn't the answer he expected. What did that even mean? Learn how to be happy? He could handle her telling him he had to be more responsible, or even that he had to be nicer, but happy? Where the hell did she get that? This had to be some bullshit answer to ease the blow. 

“Jess, you said it yourself. Everything else is muted, right?”

“Rory I’m functioning, I’m not this sad sack–”

“But you kind of are, aren’t you? Sad, at least?”

His face hardened, mouth twisting up. He looked betrayed, like he didn't trust her. Rory scrambled for the right words, he was taking it all wrong.  She took a stabilizing breath.

“You need to be able to make yourself happy before you add me to the equation, not the other way around,” she said firmly. Hearing it aloud it sounded like a cliche brushoff. 

“Dr. Phil called, he wants his cue cards back,” Jess scoffed. 

“It’s too much pressure Jess!” she broke, exasperated with his defensiveness. Her voice climbed. “I can’t handle having a person, especially one I love, needing me to not feel like shit!”

His eyes widened, softened. 

“Do you not want to deal with me? Do you want something easier?” he asked, quiet now. And it made her want to sob, how young he looked.

“No! Jess, I just think you deserve to be able to make yourself happy too. To find your place in the world. I’m not saying you have to do it alone. But I can’t be the only thing.” 

He wasn’t arguing out of anger now, he was arguing to keep her.

“You’re not the only thing. You forget I like to read? Movies? Thai food?”

“That’s pleasure Jess. But what about joy? Can you give that to yourself? Can you let yourself have it when it’s not from me?” 

That struck him, a breath falling hard from his lips. He thought about all the times he fell to hedonism. It was always paired with austerity. Drink, be up at six, work hard and angry. Have sex, hit all the right spots, don’t enjoy it too much. Don’t let go. With Rory, the laughing came easy. The joy. Did he punish himself without her? Then why did he always seem to do the selfish thing? It was all accumulating in his head too fast, he couldn’t sort it. 

“I think, I kind of get it. I don’t agree with all of it. But I get it.” 

He looked resigned, cagey, sad. He looked down, hands clenching and unclenching like they did on the pier. She knew what that meant now, that he was struggling to keep it in. Maybe one day she would know what _it_ was.

“Just, forgive yourself. And come back to me. Promise you’ll come back to me.”

It felt daunting, but it also meant this wasn't the end. He looked up at her. As much as he always felt like the one chasing, even when he was running way, here she was looking at him with begging eyes. He nodded. A sure nod.

With that she brought him in close for a desperate hug. He buried his face in her shoulder and took a long breath. After while he muttered something, muffled and bratty in her sweater 

“Bad Religion brings me joy.”

“Shut up Jess,” she laughed, tearily.

. . .

The moment for them to get into separate cars came and went. Rory cried all the way to her mom's, but it wasn't an altogether sad cry. She knew her mom was waiting for her, probably pissed and desperate for answers. Rory hadn't told her much.

Jess didn't drive long before pulling over, realizing as much as he loved it he didn't want to go back to New York. The city had too much attached to it, he couldn't think clearly. He didn't own much, and it was all in his trunk. When he had packed for the wedding, something in him said to take everything. Just incase. Just incase Rory said yes to running away with him. But here he was at the end of it, not quite rejected but definitely alone. He had been in this position before, no plan and nowhere to go. But it didn't feel desperate now, like the world had kicked him to the curb. It felt like an invitation. 

  
  



End file.
